Carbamic-acid ester and process of making same.



N TE sTArEsPArENT OFFICE.

AUGUSTUS BIsoHLiiR, or BA's'EL, SWITZE LA D, ASSIGNOR To THE .FIRM

OF BASLE CHEMIGAL,WOR KS OF BASEL, SWITZERLAND. .QARBAMIC-A CID ESTElR AND PROCESS o'F- MAKING sAilnE.

no saaioo.

lol-1.3-Dialkyl-Ethers and aTrocbss for the Manufacture of the Same, of which the following is a full, clear, and exact specification.

The pyrogallol-l.3-dialkylsethers may easilylbe oxidized to coerulignone bf manifold oxidizing agents and also by bacteria or in the organism. 11% however, the hydroxyl-.

h drogen atom of p a'ced by a-carbonic-acid radical compounds ast to oxidizing agents are, obtained.

Among the carbonic-acid derivatives of the pyro allOlslB-dialkyl-ethers, the carhe pyrogallol-ethers is rebamic-aci esters are distinguished by a ar- I tieularly good antitubercular action w en tried upon animals. f Indeed, this influence was far more favorable than the antitubercularaction of the pyrogallol-ethers themselves.

The carbamic-acid esters of the pyrogallol- '1.3'-dialkyl-ether's are obtained by treatin the pyrogallol-l.3-dialkyl-ethers with chlori of carbamic acid:

ooH /OOH ca o r i h-tclooumfo,rr, gp l-m,+1ro1.

Example: To a solution of one hundred and fifty-four parts pyroghllol-lB-diniethylother in dry ether an ethereal, solution ofeighty arts of carbamie-acid chlgrid is adde Whi e cooling and well stirring. After standing for several hours the separated crystals are filtered off, washed wit water, and

Specification of Letters Patent. l

' Application filed August a, 1906.. Serla1No.329.890

recrystallizedfromalcohol. Inthis manner grade are obtained.

The earbam'c-acid ester of py'rogalloi-"dimethyl-ether melts at 148 to 152? centi- On further heating, however, the 1 The car-' grade. melt stiffens to a white mass. bamic-acid ester is soluble in boiling water to aboutfour per cent. and crystallizes almost quantitativel on the cooling of the solution in the form 0 colorless needles. It is almost insoluble in ether, slightly soluble in hot benzene, and easily soluble in hot alcohol. By

Patented Dec. 25, 1906. l

-white needles nielting at 148 to152 centiheating with alkalies the carbamic-acid ester is easily split into pyrogallol-dimethyl-ether,

dioxid of carbon, and ammonia;

What I claim is- 1. The described process for the manufac ture of carbamic-acid esters of pyrogalloll.3-dialkyl-ethers by treating a pyrogalloldialkyl-ether with carba'mic-acid chlorid.

'2. As a new article of manufacture the de scribed carbamic-acid ester of pyrogallol 1.3-dimethyl-ether, which constitutes white to colorless needles melting at 143 to 152 centigrade soluble in boilin water, almost insoluble in ether, slightly so uble in hot ben-r zene and, easily soluble in hot alcohol and which is designed to be employed as a remedy against tuberculose.

In witness whereof I have hereunto signed my name, this27th da of July, 1906, inthe I presence of two subseri i witnesses AUGUST S "BISCHLER.

Witnesses: v g

- GEO. GIFEORD, .AMAND BRAUN, 

